- Palladium-catalyzed asymmetric allylic alkylations of polynitrogen- containing aromatic heterocycles
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We report the palladium-catalyzed asymmetric allylic alkylation (AAA) reaction of a variety of nitrogen-containing aromatic heterocycles, including pyrazine, pyrimidine, pyridazine, quinoxaline, and benzoimidazole derivatives. The mesityl ester, whose steric bulk prevents competitive deacylation of the electrophile from "hard" nucleophiles, is introduced as a new leaving group in allylic alkylation chemistry. In contrast to our previous studies of AAA reactions with pyridine-based substrates, no precomplexation with a Lewis acid is required before deprotonation with LiHMDS, underscoring the relative acidity of these electron-deficient nucleophiles.
- Trost, Barry M.,Thaisrivongs, David A.,Hartwig, Jan
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supporting information; experimental part
p. 12439 - 12441
(2011/09/16)
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